My husband and I are traveling to Italy in June with four other couples, all adults. The trip has been in the planning for nearly a year. Our first decision was to base ourselves in Tuscany for most of the trip. The next decision we had to make was villa vs. agriturismo. Whichever we picked, we wanted to reserve it early. Beautiful places with many positive online reviews become popular and get booked early. I had fun looking online at villas and found many stunning ones that would hold all of us. I believe I probaby started with VRBO and Home Away, two vacation rental home websites I'm very familiar with, but I quickly found others. But because we were planning so far in advance, well before airfare could be booked, and I know that things can happen to spoil travel plans, I ended up having some concern about booking a villa. If we reserved one with five bedrooms, and then only three or four couples went through with plans to take the trip, the villa would end up too big and too expensive for those going. So we'd have to cancel it, possibly incur some cancellation penalties if a deposit had to be paid, and then search again for a smaller place, with many of the nicest villas by then possibly having no more vacancy. It appears you might have the same issue, as you say your group size will be 8 to 10. Booking an agriturismo solved these issues. We are staying at Agriturismo Cretaiole near Pienza. We booked a three bedroom apartment and two one bedroom apartments. The agriturismo's cancellation policy is that apartments can be canceled with no penalty up until six months prior to arrival. We figured we'd be buying airline tickets about 8 to 10 months prior to our travel dates, meaning that if by then one or two couples decided the trip wasn't going to work out for them, we could cancel one or both of the one-bedroom apartments at that time, without penalty. All ten of us now have our airline tickets, so a 5 BR villa would have worked, after all, but we are very happy with our decision to stay at Agriturismo Cretaiole. We believe this is going to provide us with a richer cultural experience than we'd have in a totally independent stay in a villa. An agriturismo is like a "hosted" stay in that the owers/proprietors can help guests decide where to go and what to do, provide directions, make reservations, and often offer activities of their own. I've heard wonderful things about how warm and friendly the owners of our agriturismo are. Connecting with local people can be the most rewarding part of travel. After flying into Rome, we will stay one night in Orvieto before our drive up to the agriturismo. We were going to take the train from Rome to Orvieto, be car-less for that first day and night, and rent 3 cars in the morning from the Hertz station in Orvieto for our drive up to the agriturismo. We've been talked out of that plan. Apparently the Hertz rental location near Orvieto is very small. If we wanted one or more of the cars to have automatic transmission, for example, we might be out of luck getting one there, even if told in advance that an automatic was reserved for us there. We are just going to rent our cars right at FCO. I'd worry about driving up to the agriturismo while jet lagged, but on that first day, we're only going as far as Orvieto.
